The Amaryllidaceae alkaloid Pretazettine has recently been shown to possess significant in vitro and in vivo Anticancer and Antiviral activity. We propose, therefore, to develop and execute an efficient, stereoselective total synthesis of pretazettine which can be easily modified for the preparation of a wide variety of pretazettine analogs. Special emphasis will be placed upon the synthesis of pretazettine derivatives which are expected to be more stable in vivo and more lipophilic than pretazettine itself since such compounds should exhibit enhanced biological activity. The closely related alkaloid precriwelline will also be prepared. Having accomplished these initial objectives, adequate quantities of these coopounds will be made available for further biological screening and evaluation. In the course of these investigations, efforts will also be directed toward the invention and discovery of new, chemical reactions and procedures. For example, new general synthetic methods for the construction of quaternary carbon centers will be developed. Efforts will also be directed toward developing techniques for the enantioselective generation of fully-substituted carbon atoms.